2. Heterocyclic Polymers
N R
N N N N
N
N
N N n
• Hybrid PPP-PPV Analog
As well as other polymers containing heterocyclic systems, such as:
R2
N N
R1 R2 R1 R2 R1 R3
N N N N
• Pyrazines • Pyridines • Triazoles
Naval Air Warfare Center Weapons Division, Chemistry and Materials Division, Polymer Science &
Engineering Branch
3. Hybrid PPP-PPV Analog
O
NaI, AcCl i.) iPrMgCl
Br Br Br I Br
N CH3CN N
ii.) DMF
N H
O N
aniline
Br Br
N H N
N
N N KO But N Br
Br
N N Br N
DMF
N
O O
N B B N O
N Br O O N B
O O
Br N Pd(OAc)2, KOAc B N
N DMF O N
Naval Air Warfare Center Weapons Division, Chemistry and Materials Division, Polymer Science &
Engineering Branch
4. Hybrid PPP-PPV Analog
O SOCl2 O H2NNH2 O
Br Br Br
N OH N Cl N NHNH2
NN
O 2-ethylhexylamine O SOCl2
Br Br N
N Cl N NH Br N N Br
O
Br
N NHNH2
NN N O N N
N N B Pd(PPh3)4 N
Br N N Br O O N N N
B N N
O N N N
NaHCO3
n
THF
Naval Air Warfare Center Weapons Division, Chemistry and Materials Division, Polymer Science &
Engineering Branch
5. Supercapacitor Devices
Naval Air Warfare Center Weapons Division, Chemistry and Materials Division, Polymer Science &
Engineering Branch
6. Charging Process in Electroactive Polymers
Rudge et al., J. Power Sources 1994, 47, 89-107.
Naval Air Warfare Center Weapons Division, Chemistry and Materials Division, Polymer Science &
Engineering Branch
7. Knowledge, Skills, and Abilities
Enhanced or Obtained via this Research
• Design and synthesis of: small molecule organics, mostly heterocyclics, and polymers.
• Characterization of materials through a variety of techniques: NMR, mass spectrometry,
elemental analysis, cyclic voltammetry, galvanometry, multiple microscopy methods, etc..
• Purification of materials via: column chromatography, preparative thin layer
chromatography, medium pressure chromatography, ambient pressure and vacuum
distillation, reprecipitation, recrystallization, and sublimation.
• Structure-property / structure-function relationship studies.
• Data analysis using a variety of software: Excel, Origin, etc..
Naval Air Warfare Center Weapons Division, Chemistry and Materials Division, Polymer Science &
Engineering Branch
8. NAWCWD – Acknowledgements
Naval Air Warfare Command Weapons Division
Research Advisers Research Group
David J. Irvin, Ph.D. Adam Closson, Ph.D.
Jennifer A. Irvin, Ph.D. Justin Debord, Ph.D.
David Witker, Ph.D.
Collaborators
John Stenger-Smith, Ph.D. – NAWCWD
John Reynolds, Ph.D. – University of Florida
Fred Wudl, Ph.D. – University of California, Los Angeles
Tobin Marks, Ph.D. – Northwestern University
Greg Less, Ph.D. – T/J Technologies – Ann Arbor, MI
Funding was provided by:
• American Society for Engineering Education Postdoctoral Fellowship
• Supercapacitor Congressional Advertisement 2005
Naval Air Warfare Center Weapons Division, Chemistry and Materials Division, Polymer Science &
Engineering Branch